55 Chisholm Street, Oakville, ON L6K 3H6
It is rare to find a home that respects its history while boldly defining its future. Set within Oakville's prestigious West Harbour neighbourhood, 55 Chisholm Street is a study in modern heritage, where a century-old stone foundation anchors a home defined by thoughtful design and sustainable innovation. Superior craftsmanship and comfortable, functional spaces create a residence that is both considered and effortlessly livable. Every detail reflects a singular vision. The architecture bridges past and present with quiet confidence, pairing natural plaster walls and custom ironwork with a sculptural three-dimensional stairwell and a professional Valcucine kitchen outfitted with integrated Miele appliances. A striking soapstone fireplace grounds the main living area, while open-concept spaces extend toward landscaped gardens, creating a seamless connection between indoors and out. Its intelligence is expressed through restraint. Geothermal heating, energy-recovery ventilation, and rainwater harvesting are fully integrated, supporting a high level of performance without compromising design integrity. Upstairs, three well-appointed bedrooms and two bathrooms offer calm and privacy. The primary suite opens to a private terrace, while a treetop lookout captures elevated views across the neighbourhood canopy. The lower level includes a modern gym, cedar-lined wine cellar, and guest suite. Outside, the grounds continue the experience with a cedar sauna, outdoor shower, fire pit, and full outdoor kitchen. Steps from the lake and Downtown Oakville, this is a legacy property reimagined for the next century, offering a rare balance of architectural integrity, modern performance, and quiet, enduring livability.
Dining Room
6.52 x 4.27
Main
Family Room
4.13 x 4.21
Main
Kitchen
3.68 x 3.92
Main
Living Room
7.11 x 6.48
Main
Mud Room
3.74 x 2.37
Main
Solarium
2.32 x 4.32
Main
Bedroom
3.8 x 4.26
Second
Bedroom
5.36 x 4.26
Second
Primary Bedroom
6.28 x 3.99
Second
Bedroom
3.37 x 3.36
Basement
Laundry
10.15 x 5.47
Basement
Recreation
6.59 x 8.31
Basement
Other
3.42 x 2.63
Basement
Interior features
Air Exchanger, Countertop Range, ERV/HRV, Built-In Oven, Sauna, Ventilation System, Water Heater Owned
Basement
Full, Finished
Bathrooms
1 × 2-piece — Main, 2 × 4-piece — Second, 1 × 4-piece — Lower
Fireplace
Yes
Family room
Yes
Kitchens
1
Rooms (above / below grade)
11 above, 0 below
Approximate age
100+
Architectural style
2-Storey
Construction materials
Stucco (Plaster), Wood
Foundation
Poured Concrete, Stone
Roof
Metal
Exterior features
Lawn Sprinkler System, Landscape Lighting, Deck, Privacy, Recreational Area, Porch, Year Round Living, Patio
Direction faces
East
Garage type
Detached
Garage spaces
1
Total parking spaces
3
Driveway parking
2
Parking features
Private Double
Lot size
89.5 x 80 ft
Cross street
Lakeshore Rd W / Chisholm St
Directions
Lakeshore Rd W / Chisholm St
Neighbourhood
1002 - CO Central
Heating
Radiant — Ground Source
Cooling
Other
Water
Sewer
Sewer
List price
$3,850,000
Original list price
Annual taxes
$17,811
Tax year
2025
Assessed value
$2,134,000
Assessment year
2026
Legal description
PT LT 6 & 8, BLK 72, PL 1, AS IN OC19959 TOWN OF OAKVILLE
Inclusions
Exclusions
MLS #
W13018186
Status
Active
Transaction type
For Sale
Property type
Residential Freehold
Property sub type
Detached
Days on market
List date
Possession
Flexible
Occupancy
Owner
Listing brokerage
Sotheby's International Realty Canada, Brokerage
Co-listing brokerage
Sotheby's International Realty Canada, Brokerage
$1,923,500
Median list price
20
Active listings
New in last 30 days
Median days on market
Estimated monthly payment
$18,457
Educational estimate only — actual payment depends on your lender, credit, and insurance requirements.
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